10 of the Greatest Essays on Writing Ever Written

If there’s one topic that writers can be counted on to tackle at least once in their working lives, it’s writing itself. A good thing too, especially for all those aspiring writers out there looking for a little bit of guidance. For some winter inspiration and honing of your craft, here you’ll find ten great essays on writing, from the classic to the contemporary, from the specific to the all-encompassing. Note: there are many, many, many great essays on writing. Bias has been extended here to personal favorites and those available to read online. Also of note but not included: full books on the subject like Anne Lamott’s Bird by Bird, Stephen King’s On Writing, and Ron Carlson’s Ron Carlson Writes a Story, or, in a somewhat different sense, David Shields’ Reality Hunger, for those looking for a longer commitment. Read on, and add your own favorite essays on writing to the list in the comments.

“Not-Knowing,” Donald Barthelme, from Not Knowing: the Essays and Interviews of Donald Barthelme. Read it here.

In which Barthelme, a personal favorite and king of strange and wonderful stories, muses on not-knowing, style, our ability to “quarrel with the world, constructively,” messiness, Mallarmé, and a thief named Zeno passed out wearing a chastity belt.

“The not-knowing is crucial to art, is what permits art to be made. Without the scanning process engendered by not-knowing, without the possibility of having the mind move in unanticipated directions, there would be no invention.”

“Fairy Tale Is Form, Form Is Fairy Tale,” Kate Bernheimer, from The Writer’s Notebook: Craft Essays From Tin House. Read it here.

Bernheimer is a constant champion of the fairy tale and its influence on literature at large (not least as editor of The Fairy Tale Review), and a writer we couldn’t do without. This essay unpacks the formal elements of fairy tales, and does a fair bit more than hint at their essentialness to writers of all kinds.

“Fairy tales hold a key to the door fiercely locked between so-called realism and nonrealism, convention and experimentalism, psychology and abstraction. A key for those who see these as binaries, that is… Every writer is like a topsy- turvy doll that on one side is Red Riding Hood and on the other side the Wolf, or on the one side is a Boy and on the other, a Raven and Coffin. The traditional techniques of fairy tales—identifiable, named—are reborn in the different ways we all tell stories.”

“Reflections on Writing,” Henry Miller, from The Wisdom of the Heart. Read a few excerpts here.

A characteristically wonderful exploration of Miller’s own emotional, psychological, and technical struggles with writing.

“I had to grow foul with knowledge, realize the futility of everything; smash everything, grow desperate, then humble, then sponge myself off the slate, as it were, in order to recover my authenticity. I had to arrive at the brink and then take a leap in the dark.”

“The Figure a Poem Makes,” Robert Frost, from Collected Poems. Read it here.

A gorgeous mini-essay from an American giant that is equally relevant to writers of poetry or prose, and is almost a poem itself.

“No tears in the writer, no tears in the reader. No surprise for the writer, no surprise for the reader.”

As much about criticism as it is about writing (and perhaps more), Sontag dissects style versus form versus content versus the conceptions of all these things that we have in our heads.

“In other words, what is inevitable in a work of art is the style. To the extent that a work seems right, just, unimaginable otherwise (without loss or damage) , what we are responding to is a quality of its style. The most attractive works of art are those which give us the illusion that the artist had no alternatives, so wholly centered is he in his style. Compare that which is forced, labored, synthetic in the construction of Madame Bovary and of Ulysses with the ease and harmony of such equally ambitious works as Les Liaisons Dangereuses and Kafka’s Metamorphosis. The first two books I have mentioned are great indeed. But the greatest art seems secreted, not constructed.”

“Tradition and the Individual Talent,” T.S. Eliot, from The Sacred Wood. Read it here.

Whether or not you subscribe to Eliot’s “impersonal theory” of poetry, or his conception of the artist’s inevitable “self-sacrifice” to the past, there’s no arguing that this essay is a barn-burner.

“If you compare several representative passages of the greatest poetry you see how great is the variety of types of combination, and also how completely any semi-ethical criterion of “sublimity” misses the mark. For it is not the “greatness,” the intensity, of the emotions, the components, but the intensity of the artistic process, the pressure, so to speak, under which the fusion takes place, that counts.”

“The Ecstasy of Influence,” Jonathan Lethem, from The Ecstasy of Influence: Nonfictions, etc.. Read it here.

Here, Lethem discusses not just the shifty concept of plagiarism in fiction, but the anxiety of appropriating pop culture, copyright, Disney, the power of a gift economy, the idea of a “commons of cultural materials,” art of all forms. A must-read for any contemporary creator, especially if you’ve ever nicked a line from a favorite book.

“Most artists are brought to their vocation when their own nascent gifts are awakened by the work of a master. That is to say, most artists are converted to art by art itself. Finding one’s voice isn’t just an emptying and purifying oneself of the words of others but an adopting and embracing of filiations, communities, and discourses. Inspiration could be called inhaling the memory of an act never experienced. Invention, it must be humbly admitted, does not consist in creating out of void but out of chaos. Any artist knows these truths, no matter how deeply he or she submerges that knowing.”

“How to Write with Style,” Kurt Vonnegut, from How to Use the Power of the Written Word. Read it here.

Vonnegut is an enduring treasure trove of literary advice — everyone you know has seen this excellent video of the man explaining the shapes of stories — and this little essay is no different: clever, whip-smart, and told with joy.

“Why should you examine your writing style with the idea of improving it? Do so as a mark of respect for your readers, whatever you’re writing. If you scribble your thoughts any which way, your reader will surely feel that you care nothing about them. They will mark you down as an ego maniac or a chowderhead — or, worse, they will stop reading you.”

It’s hard to put together a list of great essays without including something from Orwell. So why not this one, forever quoted by anyone who has ever tried to write a novel, or wanted to?

“All writers are vain, selfish, and lazy, and at the very bottom of their motives there lies a mystery. Writing a book is a horrible, exhausting struggle, like a long bout of some painful illness. One would never undertake such a thing if one were not driven on by some demon whom one can neither resist nor understand. For all one knows that demon is simply the same instinct that makes a baby squall for attention. And yet it is also true that one can write nothing readable unless one constantly struggles to efface one’s own personality. Good prose is like a windowpane. I cannot say with certainty which of my motives are the strongest, but I know which of them deserve to be followed. And looking back through my work, I see that it is invariably where I lacked a political purpose that I wrote lifeless books and was betrayed into purple passages, sentences without meaning, decorative adjectives and humbug generally.”

But of course: the essay that has launched a thousand notebook-keepers.

“Why did I write it down? In order to remember, of course, but exactly what was it I wanted to remember? How much of it actually happened? Did any of it? Why do I keep a notebook at all? It is easy to deceive oneself on all those scores. The impulse to write things down is a peculiarly compulsive one, inexplicable to those who do not share it, useful only accidentally, only secondarily, in the way that any compulsion tries to justify itself. I suppose that it begins or does not begin in the cradle. Although I have felt compelled to write things down since I was five years old, I doubt that my daughter ever will, for she is a singularly blessed and accepting child, delighted with life exactly as life presents itself to her, unafraid to go to sleep and unafraid to wake up. Keepers of private notebooks are a different breed altogether, lonely and resistant rearrangers of things, anxious malcontents, children afflicted apparently at birth with some presentiment of loss.”